NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.09
Volume:	282.249
LogP:	2.703
LogD:	2.799
LogS:	-3.328
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.662
Synthetic Accessibility Score:	1.905
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.731
MDCK Permeability:	1.3906368621974252e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	99.8729476928711%
Volume Distribution (VD):	0.51
Pgp-substrate:	0.7996830344200134%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.745
CYP2C19-inhibitor:	0.77
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.68
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.459
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.784
CYP3A4-substrate:	0.325

ADMET: Excretion

Clearance (CL):	11.616
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.525
AMES Toxicity:	0.538
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.508
Skin Sensitization:	0.936
Carcinogencity:	0.777
Eye Corrosion:	0.027
Eye Irritation:	0.967
Respiratory Toxicity:	0.856

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC66905

Natural Product ID:	NPC66905
*Common Name:**	(E)-3-(4-Hydroxy-3-Methoxyphenyl)-1-(4-Hydroxyphenyl)Prop-2-En-1-One
IUPAC Name:	(E)-3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	CHEDQLDLYXAMNI-KRXBUXKQSA-N
Standard InCHI:	InChI=1S/C16H14O4/c1-20-16-10-11(3-9-15(16)19)2-8-14(18)12-4-6-13(17)7-5-12/h2-10,17,19H,1H3/b8-2+
SMILES:	COc1cc(/C=C/C(=O)c2ccc(cc2)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2263299
PubChem CID:	10659647
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003474] Retrochalcones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28394	Rohdea chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28394	Rohdea chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	7.83	%	PMID[478966]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC66905 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	1684
0.2-0.3	4700
0.3-0.4	11865
0.4-0.5	5542
0.5-0.6	3944
0.6-0.7	7612
0.7-0.8	6228
0.8-0.85	592
0.85-0.9	149
0.9-0.95	59
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.944	High Similarity	NPC5018
0.944	High Similarity	NPC123228
0.944	High Similarity	NPC276466
0.944	High Similarity	NPC32163
0.944	High Similarity	NPC151167
0.944	High Similarity	NPC123722
0.944	High Similarity	NPC16651
0.936	High Similarity	NPC179777
0.936	High Similarity	NPC303680
0.936	High Similarity	NPC84076
0.936	High Similarity	NPC90128
0.9291	High Similarity	NPC304622
0.9231	High Similarity	NPC144662
0.9225	High Similarity	NPC50763
0.9206	High Similarity	NPC276014
0.9179	High Similarity	NPC110419
0.9134	High Similarity	NPC203719
0.9134	High Similarity	NPC117237
0.9127	High Similarity	NPC53305
0.9127	High Similarity	NPC257589
0.912	High Similarity	NPC229084
0.912	High Similarity	NPC164778
0.912	High Similarity	NPC18984
0.912	High Similarity	NPC257976
0.912	High Similarity	NPC4181
0.912	High Similarity	NPC106659
0.912	High Similarity	NPC242372
0.912	High Similarity	NPC160900
0.9111	High Similarity	NPC229218
0.9111	High Similarity	NPC176030
0.9111	High Similarity	NPC192597
0.9111	High Similarity	NPC141817
0.9111	High Similarity	NPC169214
0.9111	High Similarity	NPC312256
0.9098	High Similarity	NPC284409
0.9055	High Similarity	NPC92207
0.9055	High Similarity	NPC127937
0.9048	High Similarity	NPC312404
0.9048	High Similarity	NPC273686
0.9044	High Similarity	NPC46161
0.9044	High Similarity	NPC254659
0.9044	High Similarity	NPC239608
0.9044	High Similarity	NPC46880
0.904	High Similarity	NPC114298
0.9032	High Similarity	NPC109083
0.9032	High Similarity	NPC189844
0.9032	High Similarity	NPC60962
0.9032	High Similarity	NPC224814
0.9032	High Similarity	NPC269843
0.9032	High Similarity	NPC14007
0.9032	High Similarity	NPC158949
0.9015	High Similarity	NPC139519
0.8978	High Similarity	NPC207732
0.8978	High Similarity	NPC142165
0.8963	High Similarity	NPC326065
0.8963	High Similarity	NPC28398
0.8947	High Similarity	NPC324929
0.8931	High Similarity	NPC111888
0.8923	High Similarity	NPC298268
0.8923	High Similarity	NPC172673
0.8915	High Similarity	NPC226661
0.8913	High Similarity	NPC157133
0.8905	High Similarity	NPC50954
0.8889	High Similarity	NPC474784
0.8889	High Similarity	NPC286573
0.888	High Similarity	NPC225245
0.8872	High Similarity	NPC204592
0.8872	High Similarity	NPC208760
0.8871	High Similarity	NPC299406
0.8864	High Similarity	NPC283823
0.8864	High Similarity	NPC159418
0.8849	High Similarity	NPC153644
0.8849	High Similarity	NPC165389
0.8832	High Similarity	NPC284556
0.8832	High Similarity	NPC301178
0.8819	High Similarity	NPC163083
0.8815	High Similarity	NPC325625
0.881	High Similarity	NPC201777
0.8788	High Similarity	NPC239302
0.8779	High Similarity	NPC123196
0.8779	High Similarity	NPC215941
0.8779	High Similarity	NPC319282
0.8779	High Similarity	NPC275724
0.8779	High Similarity	NPC137427
0.8779	High Similarity	NPC65935
0.8779	High Similarity	NPC311419
0.8779	High Similarity	NPC244246
0.8777	High Similarity	NPC160777
0.8777	High Similarity	NPC287495
0.8777	High Similarity	NPC73416
0.8777	High Similarity	NPC9370
0.8768	High Similarity	NPC471417
0.8768	High Similarity	NPC119663
0.8759	High Similarity	NPC84273
0.875	High Similarity	NPC30216
0.8723	High Similarity	NPC203747
0.8723	High Similarity	NPC474903
0.8723	High Similarity	NPC194653
0.8723	High Similarity	NPC80710
0.8723	High Similarity	NPC254702
0.8723	High Similarity	NPC139364
0.8722	High Similarity	NPC327410
0.871	High Similarity	NPC280001
0.8705	High Similarity	NPC105213
0.8705	High Similarity	NPC275278
0.8692	High Similarity	NPC281020
0.8682	High Similarity	NPC3221
0.8672	High Similarity	NPC474691
0.8667	High Similarity	NPC90431
0.8662	High Similarity	NPC92722
0.8662	High Similarity	NPC69430
0.8662	High Similarity	NPC40290
0.8662	High Similarity	NPC264550
0.8662	High Similarity	NPC333691
0.8662	High Similarity	NPC139293
0.8662	High Similarity	NPC195763
0.8662	High Similarity	NPC200060
0.8662	High Similarity	NPC102003
0.8662	High Similarity	NPC142876
0.8662	High Similarity	NPC264289
0.8661	High Similarity	NPC177291
0.8661	High Similarity	NPC194416
0.8657	High Similarity	NPC237330
0.8652	High Similarity	NPC58373
0.8652	High Similarity	NPC472969
0.8636	High Similarity	NPC285776
0.8633	High Similarity	NPC287722
0.8633	High Similarity	NPC473090
0.8615	High Similarity	NPC213552
0.8615	High Similarity	NPC120225
0.8613	High Similarity	NPC4796
0.8605	High Similarity	NPC246704
0.8601	High Similarity	NPC472279
0.8601	High Similarity	NPC58310
0.8601	High Similarity	NPC295977
0.8593	High Similarity	NPC89504
0.8593	High Similarity	NPC95485
0.8593	High Similarity	NPC274613
0.8593	High Similarity	NPC88065
0.8592	High Similarity	NPC15329
0.8592	High Similarity	NPC98809
0.8592	High Similarity	NPC476394
0.8592	High Similarity	NPC287395
0.8592	High Similarity	NPC183655
0.8592	High Similarity	NPC131451
0.8583	High Similarity	NPC295317
0.8582	High Similarity	NPC12377
0.8571	High Similarity	NPC300603
0.8571	High Similarity	NPC91694
0.8561	High Similarity	NPC241354
0.856	High Similarity	NPC185738
0.856	High Similarity	NPC150919
0.8551	High Similarity	NPC908
0.8551	High Similarity	NPC138438
0.8551	High Similarity	NPC50823
0.855	High Similarity	NPC293641
0.855	High Similarity	NPC20404
0.855	High Similarity	NPC12022
0.855	High Similarity	NPC20287
0.8542	High Similarity	NPC473201
0.8542	High Similarity	NPC78505
0.8542	High Similarity	NPC302783
0.8542	High Similarity	NPC144283
0.8542	High Similarity	NPC306011
0.8542	High Similarity	NPC256406
0.8542	High Similarity	NPC118427
0.8542	High Similarity	NPC31363
0.8542	High Similarity	NPC472838
0.8538	High Similarity	NPC280767
0.8538	High Similarity	NPC289459
0.8531	High Similarity	NPC287101
0.8531	High Similarity	NPC223579
0.8531	High Similarity	NPC183950
0.8531	High Similarity	NPC237441
0.8531	High Similarity	NPC52005
0.8531	High Similarity	NPC137062
0.8521	High Similarity	NPC93034
0.8521	High Similarity	NPC119660
0.8521	High Similarity	NPC188074
0.8521	High Similarity	NPC125449
0.8519	High Similarity	NPC471110
0.8507	High Similarity	NPC153453
0.85	High Similarity	NPC469615
0.8492	Intermediate Similarity	NPC272471
0.8492	Intermediate Similarity	NPC107588
0.8492	Intermediate Similarity	NPC137537
0.8492	Intermediate Similarity	NPC164706
0.8492	Intermediate Similarity	NPC470626
0.8492	Intermediate Similarity	NPC70744
0.8489	Intermediate Similarity	NPC472410
0.8485	Intermediate Similarity	NPC110313
0.8485	Intermediate Similarity	NPC278308
0.8483	Intermediate Similarity	NPC121522
0.8483	Intermediate Similarity	NPC39732
0.8483	Intermediate Similarity	NPC245382
0.8483	Intermediate Similarity	NPC477231
0.8483	Intermediate Similarity	NPC209487
0.8483	Intermediate Similarity	NPC291802
0.8483	Intermediate Similarity	NPC131266
0.8483	Intermediate Similarity	NPC181209

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC66905 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	986
0.2-0.3	1430
0.3-0.4	2653
0.4-0.5	1926
0.5-0.6	1154
0.6-0.7	550
0.7-0.8	142
0.8-0.85	6
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9134	High Similarity	NPD9494	Approved
0.912	High Similarity	NPD4379	Clinical (unspecified phase)
0.856	High Similarity	NPD5536	Phase 2
0.8356	Intermediate Similarity	NPD1934	Approved
0.8311	Intermediate Similarity	NPD3882	Suspended
0.8299	Intermediate Similarity	NPD2801	Approved
0.8226	Intermediate Similarity	NPD228	Approved
0.8182	Intermediate Similarity	NPD1511	Approved
0.8069	Intermediate Similarity	NPD1512	Approved
0.8056	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD3972	Approved
0.7972	Intermediate Similarity	NPD4628	Phase 3
0.7971	Intermediate Similarity	NPD1240	Approved
0.7971	Intermediate Similarity	NPD943	Approved
0.7943	Intermediate Similarity	NPD2935	Discontinued
0.7914	Intermediate Similarity	NPD230	Phase 1
0.7891	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1510	Phase 2
0.7857	Intermediate Similarity	NPD1607	Approved
0.7829	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6166	Phase 2
0.7821	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5283	Phase 1
0.7786	Intermediate Similarity	NPD447	Suspended
0.7785	Intermediate Similarity	NPD824	Approved
0.7778	Intermediate Similarity	NPD1876	Approved
0.7763	Intermediate Similarity	NPD3817	Phase 2
0.7762	Intermediate Similarity	NPD2344	Approved
0.7754	Intermediate Similarity	NPD3027	Phase 3
0.7722	Intermediate Similarity	NPD3818	Discontinued
0.7674	Intermediate Similarity	NPD1241	Discontinued
0.7673	Intermediate Similarity	NPD7054	Approved
0.7671	Intermediate Similarity	NPD2354	Approved
0.7667	Intermediate Similarity	NPD3455	Phase 2
0.7655	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD9545	Approved
0.7625	Intermediate Similarity	NPD7472	Approved
0.7625	Intermediate Similarity	NPD7074	Phase 3
0.7616	Intermediate Similarity	NPD4380	Phase 2
0.7586	Intermediate Similarity	NPD1549	Phase 2
0.7582	Intermediate Similarity	NPD1465	Phase 2
0.758	Intermediate Similarity	NPD6232	Discontinued
0.7568	Intermediate Similarity	NPD6799	Approved
0.7566	Intermediate Similarity	NPD6386	Approved
0.7566	Intermediate Similarity	NPD6385	Approved
0.7551	Intermediate Similarity	NPD6190	Approved
0.7551	Intermediate Similarity	NPD2309	Approved
0.755	Intermediate Similarity	NPD7458	Discontinued
0.7547	Intermediate Similarity	NPD7473	Discontinued
0.7536	Intermediate Similarity	NPD2798	Approved
0.7535	Intermediate Similarity	NPD1933	Approved
0.7518	Intermediate Similarity	NPD1283	Approved
0.7517	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD9269	Phase 2
0.75	Intermediate Similarity	NPD3022	Approved
0.7483	Intermediate Similarity	NPD8166	Discontinued
0.7469	Intermediate Similarity	NPD6797	Phase 2
0.7466	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1203	Approved
0.7463	Intermediate Similarity	NPD1651	Approved
0.7436	Intermediate Similarity	NPD7075	Discontinued
0.7423	Intermediate Similarity	NPD7685	Pre-registration
0.7423	Intermediate Similarity	NPD7251	Discontinued
0.7419	Intermediate Similarity	NPD5978	Approved
0.7419	Intermediate Similarity	NPD5977	Approved
0.7397	Intermediate Similarity	NPD2353	Approved
0.7397	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7808	Phase 3
0.7372	Intermediate Similarity	NPD1481	Phase 2
0.7365	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD4110	Phase 3
0.7365	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5844	Phase 1
0.7342	Intermediate Similarity	NPD5494	Approved
0.7338	Intermediate Similarity	NPD6873	Phase 2
0.7333	Intermediate Similarity	NPD4357	Discontinued
0.7329	Intermediate Similarity	NPD2796	Approved
0.7325	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6798	Discontinued
0.7324	Intermediate Similarity	NPD2313	Discontinued
0.7324	Intermediate Similarity	NPD3764	Approved
0.7315	Intermediate Similarity	NPD3887	Approved
0.7305	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1535	Discovery
0.7299	Intermediate Similarity	NPD1281	Approved
0.7299	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2821	Approved
0.7292	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2346	Discontinued
0.7279	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD7028	Phase 2
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.726	Intermediate Similarity	NPD4308	Phase 3
0.7259	Intermediate Similarity	NPD1894	Discontinued
0.7254	Intermediate Similarity	NPD7095	Approved
0.7248	Intermediate Similarity	NPD7003	Approved
0.7246	Intermediate Similarity	NPD9717	Approved
0.7246	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7819	Suspended
0.7239	Intermediate Similarity	NPD9493	Approved
0.7234	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3847	Discontinued
0.7222	Intermediate Similarity	NPD1613	Approved
0.7222	Intermediate Similarity	NPD3620	Phase 2
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD3142	Approved
0.7222	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1558	Phase 1
0.7222	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3140	Approved
0.7219	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1358	Approved
0.7206	Intermediate Similarity	NPD1357	Approved
0.7206	Intermediate Similarity	NPD9268	Approved
0.7205	Intermediate Similarity	NPD3926	Phase 2
0.7203	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3268	Approved
0.7194	Intermediate Similarity	NPD2983	Phase 2
0.7194	Intermediate Similarity	NPD2982	Phase 2
0.719	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6832	Phase 2
0.7179	Intermediate Similarity	NPD6801	Discontinued
0.7172	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD919	Approved
0.7162	Intermediate Similarity	NPD7266	Discontinued
0.7154	Intermediate Similarity	NPD9296	Approved
0.7153	Intermediate Similarity	NPD2674	Phase 3
0.7133	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6273	Approved
0.7124	Intermediate Similarity	NPD5049	Phase 3
0.7122	Intermediate Similarity	NPD2981	Phase 2
0.7118	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7411	Suspended
0.7111	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5242	Approved
0.7097	Intermediate Similarity	NPD3226	Approved
0.7095	Intermediate Similarity	NPD1551	Phase 2
0.7092	Intermediate Similarity	NPD2797	Approved
0.7092	Intermediate Similarity	NPD1470	Approved
0.7089	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD411	Approved
0.7083	Intermediate Similarity	NPD3144	Approved
0.7083	Intermediate Similarity	NPD3145	Approved
0.7081	Intermediate Similarity	NPD1247	Approved
0.708	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6234	Discontinued
0.705	Intermediate Similarity	NPD1201	Approved
0.7047	Intermediate Similarity	NPD1471	Phase 3
0.7047	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7440	Discontinued
0.7029	Intermediate Similarity	NPD4626	Approved
0.7027	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3748	Approved
0.7023	Intermediate Similarity	NPD2684	Approved
0.7006	Intermediate Similarity	NPD7039	Approved
0.7006	Intermediate Similarity	NPD7038	Approved
0.7006	Intermediate Similarity	NPD7110	Phase 1
0.7006	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3134	Approved
0.6993	Remote Similarity	NPD3018	Phase 2
0.6987	Remote Similarity	NPD2649	Approved
0.6987	Remote Similarity	NPD2651	Approved
0.6986	Remote Similarity	NPD4307	Phase 2
0.6986	Remote Similarity	NPD2979	Phase 3
0.6981	Remote Similarity	NPD5353	Approved
0.6981	Remote Similarity	NPD2296	Approved
0.6981	Remote Similarity	NPD5402	Approved
0.698	Remote Similarity	NPD2438	Suspended
0.6975	Remote Similarity	NPD7199	Phase 2
0.6972	Remote Similarity	NPD3266	Approved
0.6972	Remote Similarity	NPD3267	Approved
0.697	Remote Similarity	NPD2163	Approved
0.6968	Remote Similarity	NPD5403	Approved
0.6962	Remote Similarity	NPD37	Approved
0.6962	Remote Similarity	NPD7577	Discontinued
0.6954	Remote Similarity	NPD3060	Approved
0.6948	Remote Similarity	NPD5401	Approved
0.6948	Remote Similarity	NPD3146	Approved
0.6948	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4662	Approved
0.6948	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4661	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data